Methyl iodide → HCID 71239455, compound

HRID 2171611Notes

Reaction equation

HRID 2171611 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20][CH3:21])[C@@H:13]3[C@@H:18]([OH:19])[CH2:17][CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].[CH3:24]I>C1COCC1>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[C@@H:12]([O:20][CH3:21])[C@@H:13]3[C@@H:18]([O:19][CH3:24])[CH2:17][CH2:16][N:14]3[N:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71239417HCID 71239417, compound

Product 1

HCID 71239455HCID 71239455, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-chloro-4-((3S,3aS,4S)-4-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile as obtained in example 1 (50 mg, 0.16 mmol) in THF (3 mL) at 0° C. was added sodium hydride (13 mg, 0.33 mmol) for 10 min, followed by the addition of methyl iodide (0.015 mL, 0.245 mmol). The reaction mixture was stirred at room temperature for 2 h. Once the starting material had disappeared (monitored by TLC) reaction mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate, organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, 30% EtOAc in Hexane) provided the title compound (10 mg, 20%).

Workup

  1. custom(monitored by TLC) reaction mixture
  2. customwas quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate, organic layer
  4. washwas washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by column chromatography (silica gel, 30% EtOAc in Hexane)

Sources & evidence

ORD record
ord-335dd1aa0d474c0486c0e866b4e5a57b
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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